Director, Customer Success Operations - Remote Eligible

Director, Customer Success Operations

This is a strategic leadership opportunity for an operations-driven professional passionate about optimizing customer success organizations at scale. In this role, you will partner closely with executive leadership to drive operational excellence across customer success, support, professional services, and expansion functions. You will oversee strategic planning, performance analytics, process transformation, and AI-driven operational improvements to enhance customer retention, satisfaction, and team efficiency. The position combines data-driven decision-making, cross-functional collaboration, and executive-level communication within a fast-paced SaaS environment focused on innovation and customer outcomes. Ideal candidates are analytical problem-solvers with strong leadership capabilities, operational expertise, and a proven ability to translate complex business challenges into scalable solutions. This role offers the opportunity to influence company-wide initiatives, shape customer experience strategy, and drive measurable business impact in a collaborative and growth-oriented culture.

Accountabilities:

• Lead and manage the operational rhythm of the Customer Success organization, including executive reporting, strategic planning cycles, leadership meetings, board preparation, and organizational initiatives.
• Develop and execute annual and quarterly operational roadmaps aligned with business objectives, retention goals, customer satisfaction metrics, and scalability priorities.
• Build and maintain centralized reporting frameworks, dashboards, and analytics systems across customer success platforms to ensure data accuracy, visibility, and actionable insights.
• Create predictive retention and growth models focused on GRR, NRR, customer behavior trends, and operational performance indicators.
• Drive AI adoption and intelligent automation initiatives to improve operational efficiency, customer engagement, employee productivity, and service delivery outcomes.
• Oversee capacity planning and workforce models for onboarding, support, and customer success teams to align staffing with business demand and growth projections.
• Lead Voice of Customer programs leveraging NPS, CSAT, churn analysis, product usage data, and customer sentiment insights to improve customer experience and retention outcomes.
• Manage strategic transformation projects, process re-engineering initiatives, and cross-functional programs to reduce friction and optimize the customer lifecycle.
• Collaborate closely with revenue operations, product operations, finance, and executive stakeholders to align organizational goals and support company-wide operational initiatives.
• Mentor and guide business operations and analytics teams while fostering a high-performance, collaborative, and customer-centric culture.

Requirements:

• Bachelor's degree or equivalent professional experience in Business, Operations, Analytics, or a related field.
• Minimum of 10 years of leadership experience in Customer Success Operations, Business Operations, Management Consulting, or related operational leadership roles.
• Strong expertise in operational strategy, data analytics, process optimization, and customer success performance management.
• Proven experience leveraging AI, automation, and advanced analytics to improve operational efficiency and customer retention outcomes.
• Deep understanding of customer success metrics including GRR, NRR, NPS, CSAT, churn analysis, and operational KPIs.
• Advanced analytical and problem-solving skills with experience translating complex datasets into strategic recommendations and executive-level insights.
• Excellent written and verbal communication skills with the ability to influence executive stakeholders and cross-functional teams.
• Strong leadership presence with experience managing large-scale transformation initiatives and distributed teams in fast-paced environments.
• Experience with platforms such as Salesforce, Gainsight, CxOne, or similar customer success and CRM technologies.
• Healthcare or Healthcare SaaS industry experience is strongly preferred.
• Self-starter mindset with strong integrity, adaptability, collaborative spirit, and a passion for continuous improvement and innovation.

Benefits:

• Competitive salary range between $200,000 and $228,000 USD for Zone 1 locations, with compensation adjusted based on geographic region, experience, and qualifications.
• Eligibility for variable compensation and performance-based incentives.
• Flexible remote work environment within the United States.
• Comprehensive healthcare and wellness benefits for eligible employees.
• Access to mental health and wellbeing resources, including employee assistance programs and wellness platforms.
• Work-from-home support and technology discounts for remote employees.
• Collaborative and inclusive company culture focused on innovation, teamwork, and professional growth.
• Opportunities for leadership development, strategic influence, and career advancement within a growing organization.
• Employee-focused programs designed to support work-life balance, personal wellbeing, and long-term success.